Trouble in Paradise
Several weeks ago, I got fed up with the problems of iCloud syncing with Outlook and made the decision to switch to syncing with Microsoft Exchange. Initially, this seemed to be working out well, but I later realized that my contacts’ birthdays kept migrating to different days. Some were one day off; many were several days off.
There were some other small issues with Exchange sync on iOS–tasks didn’t sync at all, you couldn’t have contact groups, and certain contact fields in iOS were not supported, such as related people. But the birthday bug was the deal-breaker for me.
I did some research on this and what I learned is that it was a bug introduced by Microsoft which was copied into Apple’s code for Exchange sync. It was later fixed in Microsoft’s Outlook Connector for Hotmail, but Apple had never corrected the buggy code on their end–even though it has been known for more than two years.
Searching for a Sync Solution
So, I went about the task of looking for yet another Outlook <-> iOS sync solution, even if I had to pay for it. I came across Fruux, which looked promising, but then I learned that they do not yet support Outlook sync. According to a Twitter conversation I had with them, it’s something they are working on. So, I will be keeping an eye on that.
@suechastain this is because Outlook doesn’t support the CardDAV protocol, which we use. We are working on a go-around, though 🙂
— fruux (@fruux) October 31, 2012
I found a lot of great information on the Slipstick Systems website, and this is where I learned that several of the Outlook compatibility issues were resolved in the iCloud Control Panel version 2. I also found out about CodeTwo Sync for iCloud which enables you to keep your standard Outlook folders in sync with your iCloud folders in Outlook. The CodeTwo sync tool is worth looking into if you need to stay on iCloud 1.0 for some reason, but if you use iCloud 2.0, it is not necessary.
I also briefly investigated eM Client, an Outlook replacement, which advertises iOS syncing. I got as far as installing it, but decided I wasn’t ready to change my email client and learn a whole new PIM program. Plus, I learned that eM Client relies on Microsoft Exchange for sync and I was afraid it would result in the same birthday problem I was trying to resolve.
iCloud Round 2
Deep breath time… Am I really considering going back to iCloud? Yes, that is what I did.
I spent a day fixing my contacts’ birthdays, and (again) merging my contacts, calendar, and tasks back into one unified Outlook data file. I also deleted everything from iCloud–both in the cloud (icloud.com) and on my iOS devices. Then, with iCloud 2 installed, I once again enabled Contacts, Calendar, and Reminders sync for iCloud. This time, iCloud automatically changed the default data file in Outlook to be iCloud, and… it is working!
I have been doing a lot of testing with editing and syncing, and for the most part it is working very well. My newly created items in Outlook now go to the iCloud data file by default and I do not have to remember to move them to get them on my iDevices. Event and Tasks reminders no longer trigger two popup windows on my desktop, and they can be snoozed. I have not seen calendar events moving, but it will take some time to determine if this is truly improved.
iCloud 2.0 Caveats
There are still a few things that don’t work perfectly when syncing Outlook with iCloud 2.0:
- When a task reminder pops up in Outlook, you can’t right click to mark it complete. You also can’t double-click to open it. You have to find it in your tasks list to mark it completed. Or you can mark it completed in iOS and it will transfer the completed status back to Outlook.
- New tasks do not appear in the To-Do bar in the desktop Outlook. Only tasks that were created prior to enabling iCloud sync are shown in the To-Do bar.
- You can’t send email from IMAP email accounts in Outlook. If you use IMAP accounts, you will need to switch them to POP3 in Outlook in order to send mail.
After two weeks, those are the only problems I have encountered so far. If I run across any new issues, I will add them to this post.
One thing that is nice about doing sync this way is that I can have contact groups. I’m not sure if you can create the contact groups in Outlook. I created them using a free app called Savi Contacts on iOS and the groups transferred back to Outlook on my desktop.
As long as the Task/Reminder issues are not a big deal for you, and you don’t need to send email from IMAP accounts in Outlook, I would say it is safe to go back to syncing Outlook with iCloud 2.0. But, I do highly recommend reading everything relating to iCloud on the Slipstick website before making a decision. Of course, if you are not bothered by the birthday bug and lack of Tasks sync using Microsoft Exchange, that is another way to go.